While in Atlanta, Georgia, Ohio-born Kozelek became friends with Anthony Koutsos, a drummer. He then moved to San Francisco, California, adding guitarist Gorden Mack and bassist Jerry Vessel to complete the line-up for Red House Painters. After forming, the group played the San Francisco scene extensively, and recorded demos from 1989 to 1992. The band were signed to 4AD in 1992, on the strength of a demo tape passed to 4AD boss Ivo Watts-Russell by American Music Club frontman Mark Eitzel.[2]

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Journalist Martin Aston passed on a tape that Mark Eitzel had given to him. Never before or since had I received a demo that was 90 minutes long! In fact, it was quite some time before I actually listened to the whole thing all the way through. Every morning and evening, driving to and from work, I would start at the beginning, "24" (I know, I know, what more do you need to hear, right? What a song.), but only get about half way through that and whatever the second song on the tape was before arriving home/at 4AD. When I finally did listen to the full 90 minutes I called young Mark K. and left him a message. I learned later he was sitting in the bath listening to me talk. It was a perfect time for me to hear that brilliant band.

Between September 1992 and March 1995, the band released three LPs, one double LP, and one EP. Their first 4AD release was an album made up of demos entitled Down Colorful Hill. In 1993, the group came out with two self-titled records (now commonly referred to as Rollercoaster and Bridge because of their cover artwork).[1]

In early 1994, they released an EP entitled Shock Me, featuring two cover versions of an Ace Frehley-written KISS song. The introspective Ocean Beach followed in spring 1995. Founding guitarist Gorden Mack left shortly after the album's release, and he was replaced shortly thereafter by Phil Carney.

While Kozelek was beginning work on a solo project, he parted ways with 4AD after a tumultuous relationship, so Songs for a Blue Guitar was eventually released on Island Records subsidiary Supreme Recordings/Polygram in summer 1996. The album featured lengthy guitar jams and cover songs, and was the band's biggest seller in the U.S.[3] By early 1998, their sixth album was completed. However, the band was beginning to dissolve, and major label mergers during the late 1990s would leave the record in limbo; it was not until 2001 that Old Ramon was issued on the Sub Pop label.

Prior to the release of Old Ramon, Kozelek released a solo seven-song EP entitled Rock 'n' Roll Singer in 2000. The record consisted of three original acoustic compositions with minor full-band arrangements and four covers (three from Bon Scott-era AC/DC, and John Denver's "Around and Around") that further revealed Kozelek's fascination with 1970s classic rock. Six months later, Kozelek released his first solo album, What's Next to the Moon, which was made up entirely of acoustic covers of even more Bon Scott-era AC/DC songs, including re-recorded versions of the tracks that had appeared on the previous EP. The record was uncharacteristic of Kozelek (though he was prone to covering songs by his favorite artists) in that it is one of the shortest full-length albums of his to date, clocking in at just over thirty minutes. Both the EP and album were released by Badman Recordings.

In 2003, Kozelek and Koutsos, along with Geoff Stanfield and Tim Mooney, reformed as Sun Kil Moon, releasing the acclaimed album Ghosts of the Great Highway on Jetset Records. In a 2005 interview with The Onion's AV Club, Kozelek confirmed that he considered Sun Kil Moon essentially a continuation of Red House Painters, but that he changed the band name to grab the interest of critics who had got bored with, or stopped paying attention to, his previous band.[6] The move was successful, as Ghosts of the Great Highway would be his best-selling album yet.